Synthesis of 2′,3′-dideoxyinosine via radical deoxygenation

Takayoshi Torii, Kunisuke Izawa, Dae Hyan Cho, Doo Ok Jang

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A synthetic method for 2′,3′-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5′-O-diprotected-2′, 3′-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-ethylpiperidinium hypophosphite and triethylborane. Benzyl or p-methoxybenzyl protection of inosine at the N1, 5′-O-positions were effective for the ddI synthesis.

Original languageEnglish
Pages (from-to)985-988
Number of pages4
JournalNucleosides, Nucleotides and Nucleic Acids
Volume26
Issue number8-9
DOIs
Publication statusPublished - 2007 Aug 1

Fingerprint

Didanosine
Inosine
Derivatives

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Genetics

Cite this

Torii, Takayoshi ; Izawa, Kunisuke ; Cho, Dae Hyan ; Jang, Doo Ok. / Synthesis of 2′,3′-dideoxyinosine via radical deoxygenation. In: Nucleosides, Nucleotides and Nucleic Acids. 2007 ; Vol. 26, No. 8-9. pp. 985-988.
@article{7538f3130677485bab6de1416e7f122a,
title = "Synthesis of 2′,3′-dideoxyinosine via radical deoxygenation",
abstract = "A synthetic method for 2′,3′-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5′-O-diprotected-2′, 3′-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-ethylpiperidinium hypophosphite and triethylborane. Benzyl or p-methoxybenzyl protection of inosine at the N1, 5′-O-positions were effective for the ddI synthesis.",
author = "Takayoshi Torii and Kunisuke Izawa and Cho, {Dae Hyan} and Jang, {Doo Ok}",
year = "2007",
month = "8",
day = "1",
doi = "10.1080/15257770701508414",
language = "English",
volume = "26",
pages = "985--988",
journal = "Nucleosides, Nucleotides and Nucleic Acids",
issn = "1525-7770",
number = "8-9",

}

Synthesis of 2′,3′-dideoxyinosine via radical deoxygenation. / Torii, Takayoshi; Izawa, Kunisuke; Cho, Dae Hyan; Jang, Doo Ok.

In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 26, No. 8-9, 01.08.2007, p. 985-988.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of 2′,3′-dideoxyinosine via radical deoxygenation

AU - Torii, Takayoshi

AU - Izawa, Kunisuke

AU - Cho, Dae Hyan

AU - Jang, Doo Ok

PY - 2007/8/1

Y1 - 2007/8/1

N2 - A synthetic method for 2′,3′-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5′-O-diprotected-2′, 3′-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-ethylpiperidinium hypophosphite and triethylborane. Benzyl or p-methoxybenzyl protection of inosine at the N1, 5′-O-positions were effective for the ddI synthesis.

AB - A synthetic method for 2′,3′-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5′-O-diprotected-2′, 3′-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-ethylpiperidinium hypophosphite and triethylborane. Benzyl or p-methoxybenzyl protection of inosine at the N1, 5′-O-positions were effective for the ddI synthesis.

UR - http://www.scopus.com/inward/record.url?scp=36849009107&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=36849009107&partnerID=8YFLogxK

U2 - 10.1080/15257770701508414

DO - 10.1080/15257770701508414

M3 - Article

C2 - 18058522

AN - SCOPUS:36849009107

VL - 26

SP - 985

EP - 988

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

SN - 1525-7770

IS - 8-9

ER -